Is parking easy in Windsor, VA?

As of early 2026, 93% of users say parking is easy

Is a car needed in Windsor, VA?

As of early 2026, 92% of users say car is needed

Are yards well-kept in Windsor, VA?

As of early 2026, 92% of users say yards are well-kept

Is Windsor, VA dog-friendly?

As of early 2026, 91% of users say it's dog friendly

Does Windsor, VA show holiday spirit?

As of early 2026, 86% of users say there's holiday spirit

Do kids play outside in Windsor, VA?

As of early 2026, 82% of users say kids play outside

Would people walk alone at night in Windsor, VA?

As of early 2026, 79% of users say people would walk alone at night

Is there wildlife in Windsor, VA?

As of early 2026, 71% of users say there's wildlife

Are neighbors friendly in Windsor, VA?

As of early 2026, 62% of users say neighbors are friendly

Does Windsor, VA have sidewalks?

As of early 2026, 58% of users say there are sidewalks

Is Windsor, VA quiet?

As of early 2026, 55% of users say it's quiet

Are the streets well-lit in Windsor, VA?

As of early 2026, 50% of users say streets are well-lit

Are there community events in Windsor, VA?

As of early 2026, 45% of users say there are community events

Do residents of Windsor, VA plan to stay at least 5 years?

As of early 2026, 33% of users say they plan to stay for at least 5 years

Is Windsor, VA walkable to grocery stores?

As of early 2026, 23% of users say it's walkable to grocery stores

Is Windsor, VA walkable to restaurants?

As of early 2026, 17% of users say it's walkable to restaurants

What is 11066 Windsor Way estimated to be worth?

Trulia's estimated value for 11066 Windsor Way is $342,400 .

What is the price history for 11066 Windsor Way?

11066 Windsor Way last sold for $210,000 in September 2009.

Is Windsor a buyer's or seller's market?

Windsor is currently a balanced market, based on recent for-sale activity.

What do residents say about Windsor?

Residents describe Windsor, VA as easy to park in, well-kept, and dog-friendly. Most residents say you need a car. See recently sold homes in Windsor, VA .

Does 11066 Windsor Way have air conditioning?

Yes, 11066 Windsor Way has air conditioning.

How big is the lot at 11066 Windsor Way?

The lot at 11066 Windsor Way is about 0 acres (67 sq ft).

OFF MARKET

$342,400

Trulia Estimate

3 Beds
2 Baths
1,490 sqft

11066 Windsor Way, Windsor, VA 23487

Est. Refi. Payment $2,044/mo*

Refinance Your Home

Currently Off Market - Sold Sep 10, 2009 for $210,000

Home Value

Trulia Estimate

$342K

Since last month

$2K (+0.4%)

Since last year

$7K (+2.1%)

Since last sale

$133K (+63.3%)

Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +66% in the last 10 years

Month	Estimated value
2026
August 2026	$343K
July 2026	$341K
June 2026	$342K
May 2026	$347K
April 2026	$340K
March 2026	$336K
February 2026	$339K
January 2026	$333K
2025
December 2025	$334K
November 2025	$342K
October 2025	$338K
September 2025	$339K
August 2025	$336K
July 2025	$334K
June 2025	$330K
May 2025	$330K
April 2025	$332K
March 2025	$327K
February 2025	$322K
January 2025	$318K
2024
December 2024	$319K
November 2024	$322K
October 2024	$327K
September 2024	$323K
August 2024	$325K
July 2024	$327K
June 2024	$326K
May 2024	$323K
April 2024	$321K
March 2024	$317K
February 2024	$313K
January 2024	$311K
2023
December 2023	$308K
November 2023	$317K
October 2023	$308K
September 2023	$311K
August 2023	$308K
July 2023	$313K
June 2023	$318K
May 2023	$290K
April 2023	$286K
March 2023	$283K
February 2023	$277K
January 2023	$275K
2022
December 2022	$277K
November 2022	$280K
October 2022	$284K
September 2022	$280K
August 2022	$280K
July 2022	$284K
June 2022	$285K
May 2022	$285K
April 2022	$282K
March 2022	$279K
February 2022	$278K
January 2022	$277K
2021
December 2021	$274K
November 2021	$277K
October 2021	$273K
September 2021	$272K
August 2021	$270K
July 2021	$269K
June 2021	$266K
May 2021	$261K
April 2021	$257K
March 2021	$247K
February 2021	$245K
January 2021	$246K
2020
December 2020	$245K
November 2020	$242K
October 2020	$242K
September 2020	$242K
August 2020	$237K
July 2020	$237K
June 2020	$238K
May 2020	$234K
April 2020	$231K
March 2020	$230K
February 2020	$230K
January 2020	$229K
2019
December 2019	$229K
November 2019	$240K
October 2019	$236K
September 2019	$240K
August 2019	$239K
July 2019	$237K
June 2019	$236K
May 2019	$235K
April 2019	$233K
March 2019	$232K
February 2019	$230K
January 2019	$229K
2018
December 2018	$228K
November 2018	$228K
October 2018	$227K
September 2018	$225K
August 2018	$224K
July 2018	$220K
June 2018	$222K
May 2018	$221K
April 2018	$220K
March 2018	$220K
February 2018	$219K
January 2018	$219K
2017
December 2017	$217K
November 2017	$217K
October 2017	$216K
September 2017	$215K
August 2017	$214K
July 2017	$216K
June 2017	$216K
May 2017	$214K
April 2017	$212K
March 2017	$211K
February 2017	$208K
January 2017	$205K
2016
December 2016	$207K
November 2016	$204K
October 2016	$204K
September 2016	$206K

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
10419 Sylvia Cir, Windsor, VA	0.30	Single-Family Home	$410,000	01/23/26	3	2	2,141
10455 Sylvia Cir, Windsor, VA	0.23	Single-Family Home	$460,000	06/23/26	4	3	2,535
23115 Deer Path Trl, Windsor, VA	0.75	Single-Family Home	$300,000	01/27/26	3	2	1,673
11072 Wythe Dr, Windsor, VA	0.17	Single-Family Home	$507,000	06/05/26	5	3	2,997
23068 Andrew Ct, Windsor, VA	0.23	Single-Family Home	$456,500	02/25/26	5	3	2,797
24129 Johnson Ave, Windsor, VA	1.28	Single-Family Home	$315,000	08/21/26	3	2	1,225
17 Randolph Dr, Windsor, VA	1.19	Single-Family Home	$400,000	08/05/26	4	2	1,300
24 N Court St, Windsor, VA	1.28	Single-Family Home	$370,000	04/07/26	3	1.5	1,785
16 W Windsor Blvd, Windsor, VA	1.39	Single-Family Home	$225,000	12/30/25	3	2	1,076
26 N Court St, Windsor, VA	1.26	Single-Family Home	$355,000	08/26/26	4	2	1,739

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.

Address	Distance	Price	Bed	Bath	Sqft	Status
11072 Wythe Dr, Windsor, VA 23487	0.17	$507,000	5	3	2,997	Recently Sold
23068 Andrew Ct, Windsor, VA 23487	0.23	$456,500	5	3	2,797	Recently Sold
10455 Sylvia Cir, Windsor, VA 23487	0.24	$460,000	4	3	2,535	Recently Sold
10419 Sylvia Cir, Windsor, VA 23487	0.30	$410,000	3	2	2,141	Recently Sold
15 Courthouse Hwy, Windsor, VA 23487	0.57	$200,000	-	-	-	For Sale
E Windsor Blvd, Windsor, VA 23487	0.85	$175,000	-	-	-	For Sale
17 Randolph Dr, Windsor, VA 23487	1.19	$400,000	4	2	1,300	Recently Sold
26 N Court St, Windsor, VA 23487	1.26	$355,000	4	2	1,739	Recently Sold
24 N Court St, Windsor, VA 23487	1.28	$370,000	3	1.5	1,785	Recently Sold
24129 Johnson Ave, Windsor, VA 23487	1.28	$315,000	3	2	1,225	Recently Sold
66 Church St, Windsor, VA 23487	1.35	$150,000	-	-	-	Recently Sold

Local Information

Map ViewExplore the area around 11066 Windsor Way.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Single-Family Home

Built in 1999

1,490 sqft

$230/sqft

Garage

About this House

Great ranch home in quiet neighborhood on 2/3 acre corner lot. Move-in condition ready for you now. Close to schools, shopping, etc and easy access to all of hampton roads.

11066 Windsor Way, Windsor, VA 23487 is a 3 bedroom, 2 bathroom, 1,490 sqft single-family home built in 1999. It last sold for $210,000 on Sep 10, 2009. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $342,400, with a rent estimate of $2,243/month.

Home Details for 11066 Windsor Way

Interior Features
Heating & Cooling Heating: OilAir ConditioningCooling System: CentralHeating Fuel: Oil
Levels, Entrance, & Accessibility Stories: 1
Interior Details Number of Rooms: 6

Exterior Features
Exterior Home Features Roof: AsphaltExterior: OtherFoundation Type: Crawl Raised
Parking & Garage GarageParking: Garage Attached

Property Information
Year Built Year Built: 1999
Property Type / Style Property Type: Single Family Home

Community
Units in Building: 1

Lot Information
Lot Area: 67 sqft

Price and Tax history

Date	Event	Price
Sep 10, 2009 Source: N/A	Sold	$210,000
May 4, 2008 Source: Agent Provided	ListingRemoved	$265,900
Feb 1, 2008 Source: Agent Provided	Listed For Sale	$265,900

Year	Property tax	Tax assessment
2025	$1,876	$242,000

Additional Cost

Market trends in Windsor

Last updated July 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

6MoM

Around this home

Windsor Elementary School
PK-5
Public
624 Students
Isle Of Wight County Public Schools
7/10
GreatSchools Rating
Parent Rating Average
We love Windsor and so far the Elementary and Middle School are wonderful for our kids. It was the best move we made.
Parent Review
2y ago
3 Reviews

View nearby schools on GreatSchools

The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Windsor

At least 9 Trulia users voted on each feature.

93 % Say parking is easy
92 % Say car is needed
92 % Say yards are well-kept
91 % Say it's dog friendly
86 % Say there's holiday spirit
82 % Say kids play outside
79 % Say people would walk alone at night
71 % Say there's wildlife
62 % Say neighbors are friendly
58 % Say there are sidewalks
55 % Say it's quiet
50 % Say streets are well-lit
45 % Say there are community events
33 % Say they plan to stay for at least 5 years
23 % Say it's walkable to grocery stores
17 % Say it's walkable to restaurants

Sourced by Trulia users. Learn more about our methodology.

Ashley H.
Resident
6y ago
"I've lived here all my life and wouldn't move anywhere else. I love the close knit community as well as the Holiday festivities."
0
Flag
Braden38351
Resident
8y ago
"I’ve lived here for four years and love it! We are about to have our second child and wouldn’t want to live anywhere else"
3
Flag
Jennifer B.
12y ago
"I lived in this area with my children for 7 years. I like the schools and the community is very friendly. Windsor woods is a very nice area to live in. "
0
Flag

LGBTQ Local Legal Protections

Frequently asked questions about 11066 Windsor Way

What is 11066 Windsor Way estimated to be worth?
Trulia's estimated value for 11066 Windsor Way is $342,400.
What is the price history for 11066 Windsor Way?
11066 Windsor Way last sold for $210,000 in September 2009.
Is Windsor a buyer's or seller's market?
Windsor is currently a balanced market, based on recent for-sale activity.
What do residents say about Windsor?
Residents describe Windsor, VA as easy to park in, well-kept, and dog-friendly. Most residents say you need a car. See recently sold homes in Windsor, VA.
Does 11066 Windsor Way have air conditioning?
Yes, 11066 Windsor Way has air conditioning.
How big is the lot at 11066 Windsor Way?
The lot at 11066 Windsor Way is about 0 acres (67 sq ft).